Next to Rio de Janeiro, Sao Paulo is a bit like that portly, dorky fellow who represents Microsoft in those Apple vs. Windows commercials – he looks especially stuffy by comparison. Brazil’s largest city is positively one of the most unrecommended places by travellers weaving their way down South America’s gringo trail. I was lucky in Brazil’s largest city, however, to have a couple of people to help me scratch beneath the surface of Sampa – the first, an Australian who was relocating to the city with his Brazilian wife; the second, a Brazilian friend of an Argentine uni companero who happened to be a Palmeiras fanatic.

Another game of football was hardly on my wish list after Australia’s 6-nil evisceration at the hands of the Selecao in Brasilia on Saturday afternoon. A 16-hour overnight bus had brought me from the capital to Sao Paulo, seated next to a middle-aged bloke who seemed determine to haul half his life across the country on that stuffy coach, including a box of who-knows-what that severely cut into my already limited leg room. I packed up my iPod as soon as we hit the outskirts of Sampa – 90 minutes later we arrived in the bus station, such is the size of this sprawling urban monolith.

The next day I had a drink with Cesar the Brazilian Palmeiras fan in a faux Irish bar, while Rafael Nadal outmuscled Novak Djokovic in the final of the US Open on the surrounding televisions. Cesar – in a remarkably generous gesture, considering we had never before met – gifted me a fluorescent 2008 away kit signed by the entire squad, with Vagner Love’s name adorning the back, the striker’s typically Brazilian moniker the result of his apocryphal success with women during his youth career.

Cesar and two of his friend’s deftly explained the city’s footballing landscape. Palmeiras, the Brazilian Liverpool: a glorious history followed by a recent history of desperate failure. Sao Paulo, the Brazilian St Kilda: a historically low-profile outfit wearing red, white and black with a recent penchant for success. And Corinthians, the Brazilian Collingwood, because as was so eloquently explained by a Sao Paulo fan whose five years working as a pastry chef in Melbourne had given him a flawless Australian drawl, “They wear black and white, they’re fuckin’ big and fuckin’ good, and everyone fuckin’ hates ’em.”

The next night, after a few icy cold Antarticas in an unpretentious local botego next to the Clinicas metro station, we rolled down the hill to the Pacaembu – the city’s municipal stadium that Palmeiras is calling home while their Estádio Palestra Itália is under renovation. Sampa’s smart metro system proved a better option than driving to the ground – Cesar’s two friends, who spoke limited English but seemed equal parts bemused and thrilled that an Australian was making the effort to watch their famous old club play a drab Tuesday night game in the second division, were forced to pay the equivalent of $15 to a local bum to ensure their car’s ‘security’.

If the national stadium in Brasilia harked back to the 1936 Olympics in Berlin then the Pacaembu was straight out of Athens 1896, with its towering pillars and simple horseshoe design. The Pacaembu is one of those hoary old grounds where the history seeps in to the tired concrete terraces, and provided the appropriate surroundings for Cesar to don his father’s shirt from Palmeiras’ drought-breaking 1993 campaign, much like how Liverpool fans faithfully cling on to their old Adidas tops from the mid-’80s – the classic old shirts with the three stripes down the sleeve and Crown Paints or Candy emblazoned across the chest – to remind them of past glories.

While Palmeiras had been inauspiciously dumped to Brazil’s second tier, their opponents for the evening – ASA, from the country’s north-east – were punching above their weight to be there. While the two clubs do share some recent history – ASA caused a famous boil-over against the Sampa giants in the 2002 Cup – only the die-hards were in attendance for this unglamorous midweek outing, as the home side continued their slow match back towards Brazilian football’s top table. The stadium was split into four torcidas, the biggest of which called the Mancha Verde (‘The Green Stain’), who each chanted enthusiastically for ‘Porco’ (pigs), ‘Verdão’ (big green), or Italia (a nod to their heritage), and provided a distinctly different soundtrack to what I had become accustomed to in Spanish-speaking Latin America.

The respective team sheets read like they had been written by a careless English midwife who paid little attention to birth certificate misprints. Vilson, Gilson, Glaybson, Wanderson, Thallyson took the field alongside some familiar sounding names – two Tiagos, Wendel, Maicon, Serginho – and a referee called Wagner, supported by a female assistant. But the best handle belonged to Alan Kardec, named after the French founder of spiritualism, a dominant Palmeiras No.9 with a gleaming Colgate smile. Indeed it was Kardec who missed a 35th-minute penalty before redeeming himself a minute later by rifling in from the edge of the box.

The only Australian on the southern terrace spent the halftime break taking photos of the fanatical Mancha Verde and didn’t have time to retake his seat behind the goals before Porco threaded together a neat attack in alphabetical order, as Wendel laid on Wesley for the home side’s second in the 50th minute. A smart move by Kardec and Leandro set up Serginho to round the keeper and seal the victory – Palmeiras’ smart Adidas kit reflecting the gulf in class between the two teams, with the Verdão clearly bound for an imminent return to the Serie A.

For Cesar’s sake, I hope that 2013 was just a brief departure from Palmeiras’ usual service. Just 12 months earlier, Big Phil was in the dugout and the venerated São Marcos was between the sticks. In 2014, the club is due to celebrate its centenary and they will expect silverware to be added to their trophy cabinet. In the meantime, there’s nothing more they can do than beat-up on feeble second-tier opponents in such a manner.

With their car intact, Cesar’s two friends dropped me back to my hostel on the bustling Avenida Paulista for a rooftop view of Brazil’s 3-1 demolition of Portugal, which puts Australia’s rollover into perspective. If Cristiano Ronaldo couldn’t keep the Canaries under control, what hope did Lucas Neill have?